Fmoc isothiocyanate → N-(4-Ethoxycarbonyl-6-methoxypyridin-2-ylmethyl)-N'-(fluoren-9-ylmethyloxycarbonyl)thiourea

HRID 249733

Reaction equation

HRID 249733 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([O:14][CH3:15])[N:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH:16]1[C:28]2[CH:27]([CH2:29][O:30][C:31]([N:33]=[C:34]=[S:35])=[O:32])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH2:9]([O:8][C:6]([C:5]1[CH:11]=[C:12]([O:14][CH3:15])[N:13]=[C:3]([CH2:2][NH:1][C:34]([NH:33][C:31]([O:30][CH2:29][CH:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:28]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:32])=[S:35])[CH:4]=1)=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 4154759Fmoc isothiocyanateHCID 57791316Ethyl 2-aminomethyl-6-methoxyisonicotinate

Product 1

HCID 57791304N-(4-Ethoxycarbonyl-6-methoxypyridin-2-ylmethyl)-N'-(fluoren-9-ylmethyloxycarbonyl)thioureaYield 29.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.67 g (31.7 mmol) of ethyl 2-aminomethyl-6-methoxyisonicotinate (20d) were dissolved in 175 ml of toluene and treated at RT with 8.93 g (281.3 mmol) of fluoren-9-ylmethyloxycarbonyl isothiocyanate. After 15 minutes, the resulting precipitate was filtered off and dried at 50° C., 4.6 g of the title compound being isolated. The filtrate was concentrated, and the residue was taken up in DCM and washed three times with water. The organic phase was dried with MgSO4 and concentrated. The crude product thus obtained was chromatographed on silica gel (heptane/ethyl acetate 90:10→75:25), it being possible to isolate a further 8.1 g of the title compound.

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. customdried at 50° C.

Sources & evidence

ORD record
ord-63dc31fe34c04da292513138d3624b13
Source dataset
uspto-grants-2011_01
Patent number
US07863269B2

Linked notes

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